Patent CH-692200-A5 (CH)
Title: New 2-hydroxy-phenyl-tri:azine light absorbing cpds.
Inventor: HAYOZ PASCAL
IPC: C09D7/12
Filed: 1995-09-27
Abstract: 2-hydroxyphenyltriazines of formula (I) are new: E1, E2 = (Ia) or (Ib): A = -C(=O)-CR5=CH-R6; R1 = gp. (a), (b), CH2-C(=CH2)-R10; -(CH2)p-SiR11R'11-CH=CH2; -C(=O)-(CH2)q-CH=CH2 or -C(=O)-O-CH2-C(=CH2)-R10; (i) when R'3 = =O-CR8R'8-(CH2)-XA; then R1 may be 1-18C alkyl or 3-20C alkyl contg. -O-, -CO-O-, or -O-CO-; and (ii) when E1 = (Ia) and R2 and R14 are not H; then R1 may be -A; -CH2-CH(XA)-CH2-O-R7; -CR8R'8-(CH2)l-XA; -CH2-CH(OA)-R9; -CH2-CH(OH)-CH2-XA; -CHR8-(CH2)r-C(=O)- O-CH2-CH(OH)-CH2-OA and -CR8R'8-(CH2)l-C(=O)-XA; and (iii) when E1 = (Ib); then R1 may be -CH2-CH(XA)-CH2-O-R7; R2 = H, 1-12C alkyl, cyclohexyl, 3-6C alkenyl, halogen, phenyl or CF3; R'2 = 1-18C alkoxy, 3-18C alkenoxy, -OH or -O-CO-R12; R3, R'3 = H, -OH, -O-CH2-CH(XA)-CH2-O-R7; -O-R1 including the options for case (ii) above apart from the first 2; 1-18C alkyl, 6-12C cycloalkyl, 3-18C alkenyl, -OR131, halogen, CF3, phenyl, phenyl-(1-4C alkyl), -CN, (1-18C alkyl)-S(=O)t or phenyl-S(=O)t; R4, R'4, R''4 = H, 1-18C alkyl, 3-6C alkenyl, -OR131, halogen, CF3, phenyl, phenyl-(1-4C alkyl); -CN, (1-18C alkyl)-S(=O)t or phenyl-S(=O)t; R5 = H, -CH2-COOR13, 1-4C alkyl or -CN; R6 = H, -COOR13, 1-17C alkyl or phenyl; R7 = 1-18C alkyl, 5-12C cycloalkyl, 3-18C alkenyl, phenyl, phenyl substd. with 1-3 x 1-8C alkyl, 1-8C alkoxy, 3-8C alkenoxy, halogen or CF3, phenyl-(1-4C alkyl), 3-50C alkyl contg. one or more -O-, 1- or 2-adamantyl, (2-methyl)norbornyl or -C(=O)-R12'; R8, R'8 = H, 1-18C alkyl, phenyl, phenyl-(1-8C alkyl), phenyl substd. with 1-3 x 1-8C alkyl, 3-8C alkenoxy, 1-8C alkoxy, halogen or CF3; R9 = 1-18C alkyl, phenyl or phenyl-(1-4C alkyl); R10 = H or methyl; R11, R'11 = 1-4C alkyl, phenyl, phenyl substd. with 1-3 x 1-8C alkyl, 1-8C alkoxy, 3-8C alkenoxy, halogen or CF3; R12 = H, 1-18C alkyl, 2-18C alkenyl, phenyl, phenyl-(1-4C alkyl), 5-12C cycloalkyl, 1-12C alkoxy, phenoxy, norborn-2-yl, 5-norbornen-2-yl or 1-adamantyl; R13 = H, 1-18C alkyl, 3-18C alkenyl, phenyl, 5-12C cycloalkyl, 3-50C alkyl contg. one or more -O-; phenyl substd. with 1-3 x 1-8C alkyl, 1-8C alkoxy, 3-8C alkenoxy, halogen or CF3, phenyl-(1-4C alkyl), 1- or 2-adamantyl or (2-methyl)-norbornyl; R14, R15 = H, 1-18C alkyl, 3-18C alkenyl, 6-12C cycloalkyl, halogen, CF3, phenyl, phenyl-(1-4C alkyl), CN, (1-18C alkyl)-S-(=O)t, phenyl-S(=O)t or -OR131; R131 = 1-18C alkyl, 1-18C alkyl substd. with OH, 1-18C alkoxy, 5-12C cycloalkoxy, 3-6C alkenyloxy, halogen, -COOR13, -CONH2, -COHNR132, -CONR131R132, -NHCOR12, -CN, -OCOR12, phenoxy and/or phenoxy substd. with 1-18C alkyl or alkoxy or halogen, 3-18C alkenyl, 6-12C cycloalkyl, opt. substd. with 1-4C alkyl and/or -OCOR12, 3-50C alkyl contg. one or more -O- and opt. substd. with OH or -OCOR12, phenyl, phenyl-(1-4C alkyl), -COR12 or -SO2R12; R132, R133 = 1-12C alkyl, 3-12C alkoxyalkyl, 4-16C dialkylaminoalkyl or 5-12C cycloalkyl; or R132 and R133 together = 3-9C alkylene, oxaalkylene or azaalkylene; X = -NR8-, -O-, -NH-(CnH2n)-NH- or -O-(CkH2k)-NH-; k = 2-4; l = 0-19; m = 2-8; n = 0-4; p = 0-10; q = 1-8; r = 0-18; and t = 0, 1 or 2. Also claimed are: (1) a cpd. of formula (Ic): (2) a polymer obtd. by addn. polymerisation of at least 1 cpd. of formula (Id) (described below) and, opt., at least 1 further ethylenically unsatd. cpd.; (3) a process for incorporating 2-hydroxyphenyltriazines into organic polymers comprising incorporating (I) above, its 2 pref. forms below or (Ic) above by copolycondensation or copolyaddition during prepn. of a polymer or reacting (I) above, its 2 pref. forms below or (Ic) above with a polymer contg. suitable functional gps.; (4) a polymer prepd. by process (3) above comprising 0.05-50 wt.% of a (I); (5) an organic material comprising (I) above, its 2 pref. forms below or (Ic) above or any of the polymers described below as a stabiliser against degradation by light, oxygen and/or heat; (6) a process for stabilising organic materials against the harmful effects of light, oxygen and/or heat comprising adding to it a stabiliser as described in (5) above; (7) the use of (I) above, its 2 pref. forms below or (Ic) above or any of the polymers described below for stabilising organic materials against the harmful effects of light, oxygen and/or heat; (8) cpds. (I) and (Id) as described in any of Examples 1-43; and (9) the organic material (5) above as described in Examples B1 or B6.